Cuba at a Crossroads

The History of Cuba Through the Arts


Dreaming of traveling to Cuba for the past half-century? Make the dream a reality with this 7-night itinerary focused on art and culture in Havana and Trinidad.

Learn about Cuba’s complex history through the arts in Havana, the country's cultural epicenter. Even if you're not an art lover, prepare to be amazed by the cunning creativeness of Cuban artists and their responses to the general situation and the political culture of Cuba. Travel in style in a classic American car accompanied by your guide, and private art guide – art critic and curator Sussette Martínez Montero, who has played a prominent role in the city’s famous biennales and is very involved with contemporary art. Meet artists in their homes and studios for a deeper understanding of the works of art and the position of the artist in Cuba today. Pair studio visits with related tours such as a private Mafia Tour or Santeria Tour of Callejón de Hamel with specialized guides. In the evenings enjoy cocktails at historic Hotel Nacional overlooking the Malecón, the 8km-long sea wall that some say is the world’s longest bench, before dining at the best restaurants with rooftop bars. Experience Cuban nightlife like a local with cigars and rum at the Malecón or adjourn to La Fábrica de Arte Cubano (Cuban Art Factory), home to multiple gallery and performance spaces. Stroll Habana Vieja’s (Old Havana) Obispo Street by night for casual cocktails and traditional music. Finally, rest your weary head at Paseo 206, a new luxury boutique hotel in Havana’s Vedado neighborhood (like the Brooklyn of Havana).

Escape the city for the countryside to explore Cuba’s colonial past. Stopover in Cienfuegos (“The Pearl of the South”) on Cienfuegos Bay, where the City Tour includes a peek at the grand Teatro Tomás Terry and iced coffee at the eponymously named café next door. Continue to Trinidad, a UNESCO World Heritage Site and the most handsome town in Cuba. Bike or train to a local sugar plantation to understand the slave history in relation to the sugar industry. See slave quarters and understand how this system operated and the enormous impact sugar had on this area. Then explore valley life with a full-day or half-day hike to a waterfall or enjoy world-class horseback riding year-round. Switch gears at Playa Ancón, a short jaunt from Trinidad, where you can organize a fishing trip or catamaran to the Florida Keys. Trinidad is a fascinating counterpoint to Havana. In the evenings enjoy traditional music at Casa de la Música, a lively outdoor venue on the staircase beside the Iglesia Parroquial off Plaza Mayor, or venture further afield to Disco Ayala, a nightclub housed in a natural cave… a must-visit venue. Stay at Casa Amistad, a beautifully designed home with architectural atrium reminiscent of Mexico City and Buenos Aires. You’ll feel right at home with the people of Cuba, who are as warm and inviting as the climate.

Fly to Havana and back from Cienfuegos.

This program is operated in conjunction with Anthropologie Consulting, LLC (AC Journeys), a destination management company, under US jurisdiction, that has been operating travel to Cuba under the protections of authorizations by the Office of Foreign Assets Control of the Department of the Treasure.​


  • Day 1 & 5: Arrive Havana, José Martí Airport, Overnight Paseo 206
  • Day 6 & 7: Transfer to Trinidad via Cienfuegos, Overnight Casa Amistad
  • Day 8: Depart Cienfuegos, Jaime González Airport


The price for this trip is starting at $3,750.00 per person in double room accommodations.

See detailed inclusions in the full itinerary below.

Please note that the above is just a quotation and all is subject to availability.

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